


The Cupcake Bet

by Jess_eklom



Category: Gundam Wing
Genre: AU, Bets & Wagers, Crossdressing, M/M
Language: English
Status: Completed
Published: 2017-03-05
Updated: 2017-03-05
Packaged: 2018-09-28 10:19:02
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,369
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10091972
Author URL: https://archiveofourown.org/users/Jess_eklom/pseuds/Jess_eklom
Summary: AU - The boys are collage-age guys who know each other from their online gaming. They decide to meet at a convention, but not before Quatre falls prey to a bet that has him dressing like a maid.





	

**Author's Note:**

> RP that has been edited to read like a fic. 
> 
> The first part starts with a chat-style dialogue before transitioning into prose.   
> Posted (JUST IN TIME!) in honor of 3x4 day!

WinnerBoy - FUCK! I can't believe you WON that!!! Dammit. You'd better savor the moment, Nanashi. It won't happen again! What were the terms we agreed on again? I'd bring you a cupcake?

Death4U - Nice try, Winner. You have to bring him a cupcake in COSPLAY! Yeah Baby! FuCon here we come!

WinnerBoy - Shut it, D! No one asked you. Get the F off my private server!

Nanashi: Cupcake. A SPECTACULAR one, too! And in cosplay, LoserBoy. *troll face*

Nanashi: And as specified, a Vanilla one. I don't do that chocolate bull.

WinnerBoy: Fine, I'll get you a cupcake. Do I have to dress up?

Wing0 - Yes.

Nanashi: I'm still deciding on what.

WinnerBoy - WHO the hell invited YOU?!? Did D let you in?! 

Wing0 - No. I let him in.

Nanashi: Death4U you've seen WinnerBoy in rl, right? What could be pull off? I don't want to embarrass ourselves.

Nanashi: But I'm totally thinking a maid outfit, host-club style btw

Death4U - LIES! *I* did the hacking!! And you should totally make him crossdress, Nash.

Nanashi: yeah? That would be cool. Should I make him wear the garter belt and everything?

Nanashi: Yes, I've decided, Maid outfit. Cross dress. Bring me my cupcake on a PLATTER, host-club style, and that's what I need to satisfy my bet. I'll leave the accessories to you, WinnerBoy, but you'd better rock my world.

WinnerBoy - I swear, D. I. Will. KILL. YOU. 

Death4U - YES! He'd look hot in that. Make him wear tiny underwear too. And MJs. I swear, he's going to look totally fuckable

\- WinnerBoy has locked Death4U out of the server game -

  


The con was busy and bustling, and Trowa had very much enjoyed the whole first day. He hadn't stopped getting pictures taken of him, though... and he didn't think his Nathan Drake costume was all THAT good... He didn't even have the hair all that great. (He refused to cut his and wig itched so bad he left it for a while). But tonight was the big event as far as Trowa was concerned. Heero, Wing0, whom he had met last year at the con, was having the whole game team meet in his room tonight. 

For some reason, the most anti-social of them all somehow had met or knew all of them in person. The irony was not lost on Trowa, and so Heero offered his room for the meet up. Trowa considered changing, but, his costume was essentially ruggedly worn jeans and a T-shirt with dirt and faux zombie bits, so really, why bother changing? It wasn’t like he had a million accessories like some of the other cosplays he’d seen around. His was at least comfy enough to hang out in. 

Checking his watch, he figured he would be late if he went up to change, so instead of going to his room, he checked his phone for the room number. 

Trowa headed up the elevator and went down the hallway, glad that there weren’t very many people loitering. He went to the door with the proper number and knocked. He thought that he would be nervous, but, the truth was that he was really excited to meet his friends. His gamer buds were much closer to him than any of his real life friends at college. Trowa had a hard time talking to people, especially new people, but with his gamer tag and the anonymity of the computer, he opened up and made real and true friends like he couldn't in real life. And he was dying to meet them.

Especially WinnerBoy. Fuck! Trowa had the biggest crush on him and he sure hoped he didn't know. Duo-- Death4u-- had messaged him a few times teasing him for flirting on the game, but Trowa didn't think that Winner knew how much Trowa was totally gaga for him. Gaga... and he'd never even MET him.

Pathetic, really.  It really was, and he knew it, but that was Trowa's reality. The only thing he had to go on was Duo’s word that the guy was his relative age (as opposed to a fifty year old balding chain smoker), and that was enough. Taking a breath, he tried to calm his nerves as he waited for an answer to the door.

Heero opened the door and let him in. They were already munching on take-out, but Duo and Quatre were missing. The suite was pretty big, Trowa noted. It had a living area with a couch and a couple of chairs and then behind a wall, he presumed was the bedroom space. The place was decorated as one would expect a hotel to be, and off to the side was a door that he presumed linked two suites. He was about to ask where the rest of the group was as he took a seat, but his question was answered before he even asked.

"Duo is helping Quatre change. And buy that cupcake," the only other occupant besides Heero, another Asian, said. When Trowa gave him a curious look, the guy wiped his hands on a paper towel and extended his hand, "Chang, Wufei - DragonLord online," he introduced himself. "I'm not planning on sticking around. I can't take Duo for very long." 

DragonLord - Trowa recognized that handle. He shook his hand and gave him a nod. “Trowa Barton, Nanashi. Good to meet you.” Trowa recalled that Dragon Lord was a pretty no-nonsense kind of guy. He often took on solo missions, but he was also great at team efforts. He had to admit, he was a little jealous of his Gundam mods sometimes - particularly when his own ran out of ammo.

"Speak of the devil..." Heero muttered just as Duo practically crashed through the door that connected to the suite next door. 

"You talkin' 'bout me?" Duo grinned, flipping his long braid behind his back. "YO! Tro-by! You're here! You're going to fucking get a woody when you see him," he laughed, practically bouncing off the walls before sticking his head out the door, "Hurry the hell UP, Quat! He's here!"

Wufei groaned and rubbed the bridge of his nose. He stuffed the last bit of egg roll in his mouth and quickly ate, taking a swig of his water bottle. He was very obviously getting ready to get the hell out of there, even if Duo hadn’t been so embarrassing. 

Trowa blushed a little, looking at Heero. “Can’t you control him?” 

Heero snickered a little, "He's very.. Spirited, isn't he?" 

"You want to see spirited, how about I show you my spirit in my bed?" Duo suggested, brows waggling. 

Wufei looked offended and stood, "I'll bear witness to the bet, and then I'm GONE" he stated, looking horribly flustered. 

Trowa blushed hotter at that too. He was used to Duo being suggestive, but running his mouth like that in person was another ballgame entirely. 

"...Um... Hi Duo?" Trowa said standing. Having never actually met Death4u face to face before, he could only assume that was him because 1) he was loud, and 2) he wasn’t in a maid outfit. That seemed to get the young man’s attention enough to calm Duo right down (sort of) because he grinned and then gave Trowa a HUG. 

Trowa stiffened a little but laughed along with him, once he got over the sudden affection. When Duo finally he let him go, he turned to Heero and took his hand, entwining their fingers as they found a spot on the couch. Trowa settled into a chair then, smiling softly. He could admit, he was a bit jealous of Heero and Duo.

“Hurry UP, Quat!” Duo hollered as he sat, grabbing a carton of sesame chicken and picking through it with a pair of chopsticks. Taking a bite, his eyes fixed on the door that was slightly ajar, leading to the other room. Trowa followed his gaze, his ears picking up sounds that were coming from the other room, and waited expectantly.

In the other room, Quatre was BEYOND embarrassed! 

… But at least he didn't have to walk the con like this. 

He just had to walk from the adjacent room to the one where his friends were waiting on him. He didn’t even have to brave the hall and risk being seen, but that didn’t mean he was happy that he had to parade around in the getup. He had on a maid's dress complete with tiny black briefs, stockings, garter belt, Mary Janes, and headband. The skirt was flouncy and short and Quatre was SURE that if he bent a little at the waist, he'd flash the world. Looking very pink in the cheeks, he walked into the room with a little tray in his hands and walked right over to the one man in the room he'd never met. He couldn’t help but notice how handsome the guy was, with hair that covered part of his face and bright green eyes that threatened to root him to the spot. But a bet was a bet and Quatre didn’t back down - even if the sexiest man he’d laid eyes on was gawking at him. 

"Nanashi?" he asked, holding out the pastry, "Vanilla, per request."

Trowa had planned a few things to say when he saw him, thought he was prepared... He wasn't. He was absolutely speechless. He tried to say something, but when he opened his mouth the only thing that came out was a low sort of groan. 

Duo was right. He was hard as a ROCK, tenting his pants embarrassingly. But that wasn't all; he couldn't peel his eyes away. Winner was... was... GORGEOUS didn't even START to describe it. Trowa's brain was etching every second into his memory for instant masturbatory recall as he sat there, stunned and panting. He couldn't even SAY anything, he was too shocked at, first - how handsome a guy Winner was and second - at how HOT he was. And then all he could think of was how handsome and hot and how he was IN A MAID'S OUTFIT serving him A CUPCAKE.

Shakily, Trowa took the cupcake, managing a grunt - eloquent, Barton! He was going to try for one of those lines he’d thought up, but then the blonde’s attention was elsewhere.

"Hey Quat!" Duo called out, once Trowa had the cupcake, "C'mere a minute," he said, standing. He grabbed hold of Quatre’s wrist then commenced dragging Quatre to the bedroom of the suit and flung him on the bed. Once close enough, he then promptly flung him onto it and snapped a few quick pictures of Quatre looking disheveled with his flouncy skirt flipped up. 

Quatre tried to hop off the bed, to attack him, but laughing like a madman, Duo shoved him back down and RAN to the bathroom, locking himself in. 

"DUO! I WILL KILL YOU!" Quatre yelled, scrambling off the bed to bang on the door, "Delete that right now!!" 

Just then, Trowa's cell phone rang ... it was a text. 

_ "There. Forgive me for not getting you a birthday present?"  _ the text read - from Duo. Attached was a picture of Quatre, on his side, giving the camera a heated look with his skirt bunched up against his waist.

Trowa thought he was going to cum in his pants, holy FUCK. He hid the phone quickly so Quatre couldn't make him delete it. He was still there, in the room, with Quatre looking like THAT. Evidently, he’d given up on banging on the door when Duo didn't open up and came back to where the others were seated. 

"H-Hi..." Trowa said quietly, hoping he could at least introduce himself. 

"Hi,” Quatre said, looking embarrassed. "Can I take this off now?" 

"No. You're supposed to wear it all night," Heero said, around a mouthful of rice.

"I believe Heero is correct...” Wufei said, standing, and brushing the crumbs of an eggroll off his lap. “Now if you don't mind... I'll be going now. Winner is a man of his word."

Wufei gave them all a polite nod, then left. Heero was still snickering, but his phone rang... then rang again. He flipped it open and looked-- His expression changed to something hungry... staring at whatever was on there. He stood up abruptly, "Bye" was all he said shortly, and walked into the bedroom. He closed the door firmly behind him, still staring at the phone. 

Trowa and Quatre were stuck there now... together... Alone. 

"...S-so, so what do you bet that Duo texted Heero something naughty a minute ago?" Trowa said, wanting to break the quiet.

"Oh, no, not making any more bets against you... and I'm pretty sure Duo's found a way out of that bathroom by now." Quatre frowned, "That little bastard. I really want to strangle him sometimes."

"If it makes you feel any better, I think you look g-good." Trowa said, stammering a little. He blushed and had to look away, "...gorgeous really." he added a little bit more bravely.

Quatre blushed a little, hands fisting in the skirt he wore, trying to pull it down some, "Did he tell you to say that?"

"Who?" Trowa asked, blinking, "Duo? I just got here. You heard the four words we've exchanged, unless he said something via sign language that I missed," He said, his dry sarcasm coming out now. He was known for it online, but it also tended to offend people he didn't know so well. Damn, He shouldn't have said that to Quatre.

"I know he texts and emails you..." Quatre said, looking adorable in how shy he’d become. “You’re friends. Friends talk.”

"...Yeah. He does. But, he didn't say anything..." Trowa said, pushing his hair from his face, "I'm sorry if it bothered you, but... I meant it… You really do look gorgeous."

Quatre blushed a little, "Thanks. You look good too..."

"People have been snapping pictures of me all day! I don't think the costume is all that complicated! Not like you, you… You look really amazing...And I don’t think I’ve properly introduced myself. My name is Trowa. Trowa Barton." he said, feeling a little less shy now.

"Quatre Winner, and that does really looks good on you... I feel silly dressed this way."

"...Don't. You look sex-- Um, good."

"So... I'm supposed to stay like this for the rest of the night,” Quatre said, “What else do you want me to do?”

_ Fuck me? _ Trowa blushed but didn't say that, "Um... Um can we just… just talk for a bit..." he said a little bit flustered still. It was hard to think with Quatre there, looking SO GOOD.

Just then, Trowa’s phone buzzed again:

_ D4U: Have him sitting on your lap yet? :D _

Quatre took a seat as Trowa checked his phone and gave it a try, "Okay... how was your trip? Enjoying the con? Why a maid dress?" He REALLY was feeling uncomfortable, but a deal was a deal - even if those bastards left him to his own devices with the guy he’s been crushing on, dressed like a slut. He picked over the take out and popped a dumpling in his mouth, waiting for Trowa to reply. 

Trowa looked at the text, and then dropped the phone, spilling it on the floor right at Quatre's feet. Panicked, Trowa wasn’t even listening to Quatre as he made a dash for his phone. "Um, Um… Um it's good" he answered, bending down to get it.

Quatre grabbed the phone and handed it back, not really reading what was on it as another message popped up. 

_ D4U: I dare you! _

Trowa cursed himself - he never backed down from a dare. "...S-sit on my lap?" he asked, looking at Quatre... and then using his sexy smirk to take the edge off of it, "C'mon. You're my maid, right?"

Quatre blushed, looking completely embarrassed, "Duo put you up to this... I just know it..." he said even though he got up and sat on Trowa’s lap where he’d taken a seat nearby.

Trowa made a low sort of noise in his throat at that, GOD he felt so GOOD! 

"...So, Quatre..." he said, hands itching to touch but not wanting to just yet, "Um... How are YOU liking the con?" That was lame, but it was the best he had.

"So far so good... not many guys like us though..." he said, trying to get comfy... then suddenly he realized WHY something was digging at his hip.

"Guys like us how?" Trowa asked, trying not to get squirrely but Quatre was sitting against him THERE and oh GOD it felt SOOO fucking good! This was so wrong... but… but he couldn't bring himself to tell Quatre he should move because it felt AMAZING.

"You know... into men..." Quatre said carefully, sure that Trowa’s choice for Quatre’s outfit was a pretty good give away. DAMN, despite trying to rearrange himself something was still digging into his backside! “Are you... do you have a hard on?!?" Quatre yelped, suddenly having it click in his head.

Trowa let go of him immediately. Quatre plopped back onto the couch beside him as Trowa tried to move away, "I'm sorry! I'm SORRY! I wasn't going to do anything! You just look so good and, Fuck I can't help it!"

Quatre moved away from him a tiny bit, still sitting on the couch though, his skirt riding up just a tad, "... Was it on purpose? For me to dress this way?"

"... I... I didn't think you'd do it so WELL..." Trowa grudgingly admitted. "C'mon, wouldn't you have someone dress up in something YOU thought was sexy if you had the opportunity?! I didn't think you'd be so.... perfect. It was supposed to be funny - not hot."

Trowa’s phone buzzed again, and this time Quatre saw Duo’s handle pop up on the screen. 

_ D4U -  if you're not doing the rabbit dance, you had better be making out. Order him to!  _

"Is that Duo coaching you?" Quatre asked, honestly not sure how to feel about all this. 

Trowa handed the phone over, "...Sorta.. He's a lot bolder than I am. Go ahead, he's been doing it since I got here. I can't even think when he's sending me all this!"

Quatre only saw the last text though, "Are you going to?"

"...No..." Trowa said quietly, feeling less bold without Duo's words at the back of his head. "No, I won't, because I'd like to kiss you for real. I don’t want you to do it because I ordered you to. The whole ordering maid thing was just a joke... Wanting to meet you is real."

"Oh... " Quatre said. He was quiet for a moment then added quietly, "You should."

"...Order you to kiss me?" Trowa said, trying to get a good look at Quatre's expression, but from the angle he couldn't.

"Among other things..." Quatre said quietly. Yes, having Duo to get angry at was a good distraction, but the truth was… he had a crush on Nanashi and the idea that he’d asked Quatre to dress like that because it turned him on and not because he wanted to embarrass Quatre made him feel better about this whole crossplay thing. 

Trowa was stunned. Was he hearing things? ".... Quatre? Are you  _ enjoying _ this little game? Do you want me to play to it? I will, if you're having fun," he said, wanting to make sure he understood. But GOD did he hope he did! Having Quatre looking like a maid was hot, definitely, but having him do whatever Trowa ordered? He was going to blow his top!

"I... I am. And Duo knew I would. That's why he's been pushing buttons all day." Okay, so he hadn’t been expecting Trowa to be hard – THAT had thrown him off. He’d hoped that Trowa would harass him a bit, even if it didn’t mean anything, just so that he could have some imagination fodder later. He’d never expected Trowa to actually be INTO it like this. He’d hoped Trowa would make him pick things up, or make him sit in his lap, or make him pretend to clean - just for laughs, obviously. Just joshing between friends. It would have been funny at the time, then it could turn sexy when Quatre took the memories with him to bed. Having Trowa turned on… it threw him for a loop and now he wasn’t sure what to expect, but he  _ did _ know what he wanted. 

Trowa was quiet for a moment, then he spoke again. This time his voice was much more confident, strong and collected, "C'mere, gorgeous. Master wants a kiss."

THAT got Quatre's attention. His cock hardened in a split second and he shivered a little before crawling over to Trowa, not sure if he was meant to sit on his lap again. He then leaned in and kissed Trowa's cheek.

Trowa hummed happily, then slid down a little in the chair, "No, I said a kiss. Get on my lap…" He moved his hands, not afraid to touch now and wrapped his hand around his waist to coax him into his lap, "Now where's that kiss?"

Quatre slid onto Trowa's lap. If he were straddling him it'd make things more intimate, but he liked this game too much and he wanted to try and make Trowa say what he wanted. Quatre leaned in and kissed his lips gently, "Like that?"

Trowa’s eyes closed half-way and he hummed happily, licking his lips. "Mm, yeah. That was good, but... Master wants more." He said, eyes opening and setting Quatre with a hungry look, "Master wants a kiss like that again." He had a little smirk on his face as he said that, and had a plan forming.

Quatre blushed a little and leaned in again, kissing his lips softly, wondering how far Trowa would push it. He told himself he'd refuse if Trowa got out of hand... but so far... it was nice.

Trowa's hand moved up to touch Quatre's cheek then, and he used just a little bit of pressure to pull him closer. Trowa closed his eyes and opened his lips, sucking softly on Quatre's bottom lip and trying to get him to respond a little more. He was no pro at kissing, but he enjoyed it so much he hoped he didn't suck at it

Quatre moaned softly. He liked that Trowa was leading him like that and parted his lips, letting Trowa have more. 

He changed his mind about refusing at that moment; Trowa could have anything! "Mmm... I'll stop you if you go too far..." Quatre promised. "Or do something I don't want..." he whispered. He really intended on keeping to that last bit … but he was starting to have doubts about what he’d consider ‘too far.’

Trowa could feel his body begging for more, and he slowly put pressure on Quatre's hips to slide him over a bit, more towards the middle of his lap. He pulled away from the kiss to get some breath, licking his lips as he did, "Mmm, you're a gorgeous little thing. I'm very pleased... sit on me proper, darling," he purred, being more overt at leading him to straddle his hips.

Quatre shivered at the sexy tone of voice Trowa had taken and straddled his lap, pressing his own erection against Trowa's. He gasped and rocked into them, "Like this, Master?"

"Oh FUCK yes" Trowa moaned, his head dropping back a little. He tried to keep himself from embarrassing himself right then! Fuck! He knew he was making a wet spot in the jeans already, but he didn't care enough to do anything about it. "Yeah, yeah, darling, now get back here and give master another kiss," he ordered, using his hand to pull his jaw forward again, Trowa's eyes hungrier and his lips more impatient.

Quatre groaned and leaned in, kissing him a little more deeply. He slipped Trowa some tongue then took one of Trowa's hands and rested it on his thigh, practically at his ass. He groaned a little and kissed him deeper. He was very hot... and with Trowa's hand up his skirt? He really wanted to make the man cum.

Trowa shuddered under him, his hips rocking up almost without Trowa's permission. He couldn't stop the kiss through! He loved it too much. His hand moved slowly, touching the flesh... oh GOD it felt SO GOOD! His hand slowly, ever, ever so slowly crept upwards... upwards... and then he was holding Quatre's ass in his hands, massaging it gently and feeling the little tiny underwear and his hot flesh. Trowa shuddered harder, his hips bucking. His eyes flew open, realizing what was very nearly happening. Shit, shit… he was second away from cumming, he knew he was.

Quatre knew it was coming too and rocked against him, "Do you want to fuck me?" Quatre purred in Trowa's ear, "You'll have to trap me like this again though..."

That was IT! Quatre's voice in his ear, telling him what he wanted? Oh GOD! Trowa bucked up against him and his hand held his ass hard. A ragged moan ripped from his throat as Trowa rode the wave, over and over, he felt his body just PUMPING out, filling his pants with sticky mess as he twitched and shivered, "....Oh god, Quatre..." he moaned, eyes closing as he rode out the aftershocks, licking his lips and breathing slow, "...Oh...my...God..."

Quatre leaned in and kissed his neck, "Need to go change? "

Trowa's arms stayed around Quatre's waist, and he smile softly, "...Yeah... Is that okay?" He asked, face turning red. He had loved it, every minute, but now he realized what he'd done. He sure hoped Quatre wasn't mad...

"Only if we can play again later..."

Trowa licked his lips, "...Play like this?" he asked, looking pleased, "I'd like that. A lot."

"Then go get cleaned up," Quatre said, getting off him, "I need to shower and clean up too..."

Trowa smiled warmly, and then... moved back to him, giving Quatre a peck on the cheek before he dashed away to his own room that he was sharing with his sister and some of her friends. He hoped no one was there. 


End file.
